Chicago vacation rentals
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Top-rated vacation rentals in Chicago
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Chicago fishing vacation rentals
Apartment in Evanston
4.97 out of 5 average rating, 456 reviewsCharming, Sunny Apartment with Backyard Garden
Lovely spacious apartment with beautiful furnishings and thoughtful details. Very comfortable and nice. Very responsive hose. Would definitely stay here again.
Apartment in Lake View
4.84 out of 5 average rating, 432 reviewsLakeview Charmer -with parking!
Needing a last-minute place to stay in Lakeview over Thanksgiving weekend, Cathy's place stood out - the location and amenities (including a hard-to-find parking space) were just perfect for our needs. The cozy garden level apt. has entries from both the rear (through three doors with coded locks ) and the front and is outfitted with extras like a Keurig, regular coffee machine, YouTube TV, sound machines to mitigate train noise, snacks, etc. and a notebook with lots of information about the apt. and locale. The kitchen was adequately equipped and has a small table for four with an extra leaf available - we brought Thanksgiving dinner with us from Ohio to warm up in the oven and microwave and everything worked out great! Fabulous location within walking distance of restaurants, bars, theaters, Wrigley field, the train (took us 20 min to get downtown), etc. Cathy's communication with us was superb, with follow-up upon arrival and flexibility with check-in. Great stay - Thanks!
Bungalow in Lake View
4.94 out of 5 average rating, 102 reviewsChicago Bootlegger House Sleeps 10-20
Great spot for a big group! We were in town for a Bears game and easily accommodated 12. Plenty of beds and the hangout area was sweet.
Condo in East Rogers Park
4.92 out of 5 average rating, 219 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Kaye’s place is private, cozy, has unique decor and everything you need for a great visit. The area is walkable and safe with lots to do. I was visiting my son and new DIL. My daughter-in-law enjoyed completing one of Kaye’s puzzles. Plenty of room to enjoy hanging out with son and DIL and eat dinner there with them. This is a favorite of mine and will continue to stay while visiting family. Kaye was extremely responsive and helped me out when I needed some good advice!! Thanks so much.
Apartment in Andersonville
4.93 out of 5 average rating, 423 reviewsAndersonville Living
We had a wonderful stay at Joseph’s place in Andersonville. The beds were very comfortable, the apartment is located on a quiet street yet very near restaurants and stores. The communication with the hosts was very easy. Our family thoroughly enjoyed our stay at Joseph’s.
Loft in Lake View
4.9 out of 5 average rating, 779 reviewsUrban Chicago Loft, 1 blk to train w/ 2 pkg spots
Really enjoyed this place. It was a great location. There were three of us (one year old included.) She had no trouble adapting and thought it was amazing there were so many steps to go up. With that being said.. if you are NOT in shape or elderly.. this is NOT for you. Steps are the only way up and down.. so luggage has to be carried up. We are in great shape so it was nothing for us. However, I can see that being an issue. Jay has the easiest check in process. I felt like he was standing in front of me talking when I was reading the directions. It is extremely easy to understand and so is check out. I would love to book again in the future when there is a cubs game! The stadium is a hop and a skip away! Thank you Jay for a wonderful stay :)
Condo in Uptown
4.98 out of 5 average rating, 251 reviewsNear Lake Michigan & Wrigley Field
Fantastic place. Everything was clean, the apartment felt cozy and inviting, and there were several amenities. overall i have no complaints, if you're staying in uptown chicago, this is the one!
Home in Whiting
4.83 out of 5 average rating, 144 reviewsThe Spa of Downtown Whiting
I really enjoyed my stay while visiting Chicago. I loved the home, and everything included. Steven was a wonderful host and responded fast with any questions I had. If I ever have to come back this will always be my go to place lol.
Chicago apartment rentals
Apartment in Avondale
4.98 out of 5 average rating, 101 reviewsLovely 2bedroom 1bath Apt and outdoor seating.
It was exactly as described in the listing and conveniently located near the train station. I would highly recommend it to anyone!
Apartment in Lincoln Park
4.95 out of 5 average rating, 110 reviewsElegant Depaul Apt on Jonquil Park
This was our first time staying in an Airbnb and questions were answered quickly and kindly. We found the apartment clean, cozy, comfortable, close to many amenities, including train, and walking distance to our daughter’s apartment was convenient. We didn’t use the kitchen, except for the Keurig coffee maker and filtered water pitcher, which were nice and it was well stocked. The bed was comfortable and shower nice. Judith was a gracious host, kindly responded to text messages, and available. Thank you so much a great stay in Chicago!
Apartment in Evanston
4.84 out of 5 average rating, 244 reviewsAdorable 1BR apartment near Northwestern
This is a very nice apartment near Central Street in Evanston. The apartment was clean, very nice, and private.
Apartment in Chicago
4.99 out of 5 average rating, 190 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Brittney’s home was clean, extremely spacious and full of beautiful natural lighting. I was surprised by how quiet it was, because it’s so conveniently close to the highway. Her home exceeded my expectations.
Apartment in Roscoe Village
4.97 out of 5 average rating, 137 reviewsInviting 2 Bedroom Apartment in Roscoe Village
Lara’s place was very homey. We love the Roscoe Village area and her place was nestled within its beautiful streets. We had a great stay with our kids (they even had games, high chairs, and other kid friendly amenities). My son lovingly referred to it as our Holiday house. We would definitely stay again!
Apartment in Bridgeport
4.92 out of 5 average rating, 106 reviewsCitySlickers Crash Pad /Free Parking /No Clean Fee
The place is well equipped They provide many things even the make up remover and facial cleanser
Apartment in Logan Square
4.82 out of 5 average rating, 250 reviewsBERNARD CHATEAU - LOGAN SQUARE
Top class location lovely people to deal with, 10/10
Apartment in Jefferson Park
4.87 out of 5 average rating, 120 reviewsModern 2 bdrm apt near O'hare and Downtown
Fabio’s communication and responsiveness are outstanding. The space is clean, uncluttered. and quiet. We did have an issue with the bathtub/shower getting clogged but we contacted him and he got a plumber to come out on a Sunday without any hesitation. We appreciated a clean and comfortable place to stay. Thank you Fabio!
Chicago home rentals
Home in Berwyn
4.95 out of 5 average rating, 44 reviews5 Star Upscale Entire Family Neighborhood Home
Beautiful home well stocked with great offstreet parking. Kids loved the Fußball table! Great tv and kitchen
Home in Roscoe Village
4.93 out of 5 average rating, 261 reviewsDuplex Home RoscoeVillage/Wrigley Free St Parking
We had a fantastic stay! The space was large, clean, and perfect for our family—plenty of room to spread out. The location was excellent, with everything we needed close by. The host was incredibly responsive and made sure we had a smooth experience. We’d definitely come back!
Home in Naperville
4.88 out of 5 average rating, 126 reviewsHome away from home
Vytautas is a very welcoming, responsive host. He responded quickly to questions about the property and my stay in particular. The property is very convenient to Naperville and highways connecting to the greater area. It was easy to enter the front door and the home was toasty warm on a cold Chicago night when I arrived. It was great to have the private back yard with my dog. I think it would be fun to be there in summer when the trees have leaves and the weather is warm. The only down side for people who want to have meals there is that you have to set up a table (which is folded up in the back room) and chairs to have a group sit down. This wasn't a problem for me because I have family in the area and went to their homes for meals. And I believe the table would be large enough for 6 if you have that many people. I wouldn't hesitate to stay there again. Thank you, Vytautas
Home in Bolingbrook
4.73 out of 5 average rating, 22 reviewsSerenity King|7 min -> Hwy & Mall|Backyard
this was a great place lovely 😍 will book again and who ever reading this should book to
Home in Blue Island
4.81 out of 5 average rating, 183 reviewsWarm and comfortable inviting Suburban home !
Rich's place was the perfect location for us. We needed to get to the city for the Chicago Marathon, but didn't want to stay IN the city. Check in and check out were easy. The place was clean, spacious, and comfortable. Thank you!!
Home in Lansing
4.81 out of 5 average rating, 107 reviewsCozy at The Walter 2bd/1bath Home
The house was very welcoming and clean. There was also some food in the fridge that was provided and a nice surprise. The host was extremely accommodating, friendly, and easy to contact. We would definitely stay here if we are working in the area again.
Home in Justice
4.94 out of 5 average rating, 220 reviews3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin
It was a great place to have family dinners with a big dining room table. The kitchen was great. The bedrooms were great. Definitely recommend staying here.
Home in Homer Glen
5 out of 5 average rating, 3 reviews4 bedroom home rental in quiet neighborhood
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.
Quick stats about vacation rentals in Chicago
Total rentals
11K properties
Total number of reviews
514K reviews
Family-friendly rentals
5K properties are a good fit for families
Pet-friendly rentals
3.4K properties allow pets
Rentals with a pool
1.1K properties have a pool
Rentals with dedicated workspaces
6.9K properties have a dedicated workspace
Your guide to Chicago
All About Chicago
Settled along the banks of Lake Michigan, the Windy City of Chicago offers world-class dining, exciting architecture, a top performing arts scene, and plenty of excellent museums. With more than 200 neighborhoods calling this city home, there’s a unique aura found in each.
You’ll find historic mansions and upscale shopping in Gold Coast, Gothic-style university buildings in Hyde Park, cool cocktail bars and quirky shops in hip Logan Square, and incredible comedy clubs in Old Town. Enjoy time outside lounging on the city beaches, catch a baseball game at Wrigley Field, shop along the Magnificent Mile, or sample the celebrated dining scene in this dynamic city, the third-largest metropolis in the United States.
The best time to stay in a vacation rental in Chicago
Chicago’s summers are warm and sunny, which means the rooftops and patios are buzzing, and the days are filled with music and food festivals. This is also when the city's lakeside beaches are at their best, so it’s a popular time for booking Chicago vacation rentals. Fall is chilly but pleasant. Winters are downright cold, and you can expect plenty of snow between the months of December and April, but there’s also plenty of opportunity for ice skating in rinks and snowshoeing and sledding down hills in city parks. There are also wonderful Christmas lights at Navy Pier and throughout the city. Expect relatively cool temperatures and a decent amount of rainfall in spring, and pack your waterproof layers.
Top things to do in Chicago
The Art Institute of Chicago
The Art Institute is one of the best museums in the United States with more than 300,000 permanent artworks and many traveling exhibits. Take shelter from the city’s infamous wind and check out world-famous paintings from French Impressionists and modern American masterpieces. Cafes and restaurants are on-site for coffee breaks and leisurely lunches, and the museum also hosts regular lectures and events.
Willis Tower
The tallest building in the world for almost 25 years, the Willis Tower is a 110-story skyscraper that’s now the second-tallest building in the U.S. For a view that can reach Wisconsin and Michigan on a clear day, visit The Willis Tower observation deck. It’s located on the 103rd floor of the building, and you can even step inside glass observation boxes that extend four feet over the street below.
Millennium Park
Located across from the Art Institute, this city park is one of the most recognizable areas in Chicago thanks to the iconic Cloud Gate sculpture, lovingly known as “The Bean.” Rotating sculpture exhibitions and the naturalistic Lurie Garden make for lovely visits in spring and fall. During the summer months, the park comes alive with outdoor concerts, film screenings, dance performances, and even public yoga classes.
Frequently Asked Questions
How is the weather in Chicago?
Chicago experiences a wide range of weather, from hot summers that can reach 95°F (35°C) to chilly winters that can drop to 20°F (-6°C). The city exhibits four distinct seasons, with beautiful spring blossoms, sunny summers, colorful autumns, and snow-dusted winters, perfect for ice skating in Millennium Park.
What are some of the best things to do in Chicago?
In Chicago, you can explore iconic sights like Navy Pier, Cloud Gate in Millennium Park, and Willis Tower's SkyDeck for breathtaking city views. Cultural enthusiasts can immerse themselves in the Art Institute of Chicago or catch an engaging show at the Second City comedy club.
What is the best time of year to visit Chicago?
Summer, from June to August, is often recommended to visit Chicago. During this season, the city hosts various events, including the Chicago Blues Festival and Taste of Chicago, attracting food and music enthusiasts alike. However, the city is vibrant year-round, with winter activities such as ice skating and holiday markets.
What are the best places to stay in Chicago?
Popular areas to stay in Chicago include the vibrant neighborhoods of River North and Gold Coast for their proximity to dining and shopping. Lincoln Park and Lakeview are also often recommended for their leafy streets, local cafes, and proximity to the lake.
What are the best places to visit in Chicago?
Popular places to visit in Chicago include the culturally rich neighborhoods like Chinatown, Little Italy, and Pilsen. Navy Pier, the Magnificent Mile shopping district, as well as green spaces like Grant Park and Lincoln Park, are also frequently suggested.
What are some hiking trails in Chicago?
While Chicago is an urban city, it still has some scenic hiking trails. The Chicago Lakefront Trail, a 18-mile (29 km) path along Lake Michigan, and the North Branch Trail System in the Forest Preserves of Cook County are popular among outdoor enthusiasts.
What are some family activities to do in Chicago?
Families often enjoy exploring the Shedd Aquarium, the Field Museum of Natural History, and the interactive exhibits at the Chicago Children's Museum. A boat tour along the Chicago River, highlighting the city's architectural marvels, is another frequently suggested activity for families.
What are some of the best day trip ideas in Chicago?
For day trips from Chicago, consider a visit to the Indiana Dunes National Park for some beach fun and hiking, or explore the charming town of Geneva for a relaxed pace with boutique shopping. Rockford, with its Anderson Japanese Gardens and Burpee Museum of Natural History, is also a viable option.
What types of vacation rentals are available in Chicago?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Chicago. From over 1,080 condo rentals, over 1,900 house rentals to over 6,100 apartment rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Chicago?
Yes! Work meets play with ease at over 6,910 vacation rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.
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